(1S,2S,3E,5R,6S,11S,14S,16R,17S,18S)-15,17-dihydroxy-5,6,16-trimethoxy-2,14,18-trimethyl-11-phenyl-12,19-dioxabicyclo[13.3.1]nonadec-3-en-13-one

Base Information

• Chemical Name: (1S,2S,3E,5R,6S,11S,14S,16R,17S,18S)-15,17-dihydroxy-5,6,16-trimethoxy-2,14,18-trimethyl-11-phenyl-12,19-dioxabicyclo[13.3.1]nonadec-3-en-13-one
• CAS No.: 122547-72-2
• Molecular Formula: C29H44 O8
• Molecular Weight: 520.664
• European Community (EC) Number: 695-712-7
• Metabolomics Workbench ID: 70882
• Mol file: 122547-72-2.mol

Synonyms:soraphen A;soraphen A(1alpha)

Chemical Property of (1S,2S,3E,5R,6S,11S,14S,16R,17S,18S)-15,17-dihydroxy-5,6,16-trimethoxy-2,14,18-trimethyl-11-phenyl-12,19-dioxabicyclo[13.3.1]nonadec-3-en-13-one

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 673.1°Cat760mmHg
• Flash Point: 213.7°C
• PSA: 103.68000
• Density: 1.16g/cm³
• LogP: 3.80270
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 520.30361836
• Heavy Atom Count: 37
• Complexity: 737

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C=CC(C(CCCCC(OC(=O)C(C2(C(C(C(C1O2)C)O)OC)O)C)C3=CC=CC=C3)OC)OC
• Isomeric SMILES: C[C@H]1/C=C/[C@H]([C@H](CCCC[C@H](OC(=O)[C@H](C2([C@@H]([C@H]([C@@H]([C@H]1O2)C)O)OC)O)C)C3=CC=CC=C3)OC)OC

Technology Process of (1S,2S,3E,5R,6S,11S,14S,16R,17S,18S)-15,17-dihydroxy-5,6,16-trimethoxy-2,14,18-trimethyl-11-phenyl-12,19-dioxabicyclo[13.3.1]nonadec-3-en-13-one

There total 30 articles about (1S,2S,3E,5R,6S,11S,14S,16R,17S,18S)-15,17-dihydroxy-5,6,16-trimethoxy-2,14,18-trimethyl-11-phenyl-12,19-dioxabicyclo[13.3.1]nonadec-3-en-13-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

3-O-methylsoraphen → (1S,2S,3E,5R,6S,11S,14S,15R,16R,17S,18S)-15,17-dihydroxy-5,6,16-trimethoxy-2,14,18-trimethyl-11-phenyl-12,19-dioxabicyclo[13.3.1]nonadec-3-en-13-one (122547-72-2)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 0.25h; Ambient temperature;

Reference yield:

(E)-(3S,5R,6S,7R,8S,9S,12R,13S,18S)-6,8-Dihydroxy-5,12,13-trimethoxy-3,7,9-trimethyl-18-phenyl-oxacyclooctadec-10-ene-2,4-dione → (1S,2S,3E,5R,6S,11S,14S,15R,16R,17S,18S)-15,17-dihydroxy-5,6,16-trimethoxy-2,14,18-trimethyl-11-phenyl-12,19-dioxabicyclo[13.3.1]nonadec-3-en-13-one (122547-72-2)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 12h; Yield given; Ambient temperature;

DOI:10.1055/s-1999-3671

Reference yield:

methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hexopyranoside (64551-84-4) → (1S,2S,3E,5R,6S,11S,14S,15R,16R,17S,18S)-15,17-dihydroxy-5,6,16-trimethoxy-2,14,18-trimethyl-11-phenyl-12,19-dioxabicyclo[13.3.1]nonadec-3-en-13-one (122547-72-2)

Guidance literature:

Multi-step reaction with 9 steps

4: 90 percent / (COCl)2 / dimethylsulfoxide; CH₂Cl₂ / 1 h / -78 °C

With oxalyl dichloride; In dichloromethane; dimethyl sulfoxide;

upstream raw materials:

(E)-(1R,5S,10S,11R,14S,15S,16S,17S,18R)-1,17-Dihydroxy-10,11,18-trimethoxy-14,16-dimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-3-one

methyl iodide

(17S)-17-hydroxy-5-O-(4-methoxybenzyl)-3-O-methyl-1,17-seco-1-soraphenic acid

methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hexopyranoside

Downstream raw materials:

(3R,3aR,5R,6S,7aS)-3a,7a-Dimethoxy-3,6-dimethyl-5-((E)-(1S,4R,5S,10R)-4,5,10-trimethoxy-1-methyl-10-phenyl-dec-2-enyl)-hexahydro-furo[3,2-b]pyran-2-one

(E)-(1R,2S,5S,10S,11R,14S,15R,16S,18R)-18-Hydroxy-10,11-dimethoxy-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-3-one

(E)-(1R,2S,5S,10S,11R,14S,15R,16S,18R)-1-Hydroxy-10,11,18-trimethoxy-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-3-one

(E)-(1R,2S,5S,10S,11R,14S,15R,16S)-10,11-Dimethoxy-2,14,16-trimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-ene-3,18-dione